(4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline → HCID 58980888, compound

HRID 82769Notes

Reaction equation

HRID 82769 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[F:13][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@H:9]([CH2:14][OH:15])[CH2:10]1

Participants

3

Reactant 1

HCID 2756017(4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline

Product 1

HCID 58980888HCID 58980888, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (500 mg, 2.14 mmol) in THF (15 mL) was treated with a 1N solution of BH3-THF complex (4.29 mL, 4.29 mmol). The mixture was stirred at ambient temperature for 12 hours then quenched with MeOH and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound (425 mg, 90%). MS (DCI/NH3) m/z 220 (M+H)+.

Workup

  1. customthen quenched with MeOH
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1c747746a92a4da8bf713e8238cb2560
Source dataset
uspto-grants-2014_09
Patent number
US08846730B2

Reaction notes

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